Novel ring expansion routes are proposed to prepare 8,9,13,14-disecosteroids modecules that are related to estrone progesterone and related compounds. Much of the work is based on using siloxy-Cope or alkoxy-Cope rearrangements to effect ring expansions of benzo substituted medium-sized rings such that the specifically substituted large-ring compounds are generated. Mechanistic studies of these rearrangements are also proposed.